(E)-1-(non-1-en-3-ynyl)benzene | 111468-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(non-1-en-3-ynyl)benzene
• 英文别名: (E)-1-phenyl-1-nonen-3-yne；(E)-non-1-en-3-ynylbenzene；[(E)-non-1-en-3-ynyl]benzene
• CAS: 111468-65-6
• 化学式: C₁₅H₁₈
• 分子量: 198.308
• InChiKey: NUTVAFWFYDMCDV-FMIVXFBMSA-N

物化性质

• 沸点：
  307.0±21.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  乙基溴化镁 、 (E)-1-(non-1-en-3-ynyl)benzene 在 二氯二茂锆 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到(1E,3Z-4-ethyl-nona-1,3-dienyl)benzene
  参考文献：
  名称：

  通过醛加成α-烯基取代的氧化锆环戊烯的立体选择合成具有多个连续立体中心的β-羟基丙二烯

  摘要：

  描述了一种高度立体选择性的方法，用于通过向醛中添加α-烯基氧化锆环戊烯，合成具有多个立体生成中心（包括烯键式轴向手性以及中心手性）的β-羟基丙二烯。值得注意的是，与通常的烷基或芳基取代的氧化锆环戊烯相比，该反应的化学选择性完全不同。这意味着，CC键的形成选择性地发生在被苯基或烷基取代的烯基碳上，而在后一种情况下，通常观察到将醛插入烷基-锆键中以提供七元恶唑烷环。

  DOI：

  10.1021/jo900808k
• 作为产物：
  描述：

  苯基氯化镁 、 (E)-1-chloro-non-1-en-3-yne 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以95%的产率得到(E)-1-(non-1-en-3-ynyl)benzene
  参考文献：
  名称：

  Versatile palladium(II)-catalyzed Negishi coupling reactions with functionalized conjugated alkenyl chlorides

  摘要：

  Under palladium catalysis, we found that organozincate reagents, generated in situ, by reaction of Grignard compounds with less than molar amounts of zinc chloride, in the presence of conjugated alkenyl chlorides, give rapidly and cleanly the corresponding coupling product in high yields. In this way, aryl as well as primary and secondary alkyl substituents have been introduced successfully. The selectivity of the reaction allows to prepare various functionalized conjugated enynes and dienes from chloroenyne and chlorodiene derivatives bearing a functional group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01627-7

文献信息

• CuI-Catalyzed Suzuki−Miyaura and Sonogashira Cross-Coupling Reactions Using DABCO as Ligand
  作者：Jin-Heng Li、Ji-Lan Li、De-Ping Wang、Shao-Feng Pi、Ye-Xiang Xie、Man-Bo Zhang、Xi-Chao Hu

  DOI：10.1021/jo0623742

  日期：2007.3.1

  presence of TBAB, CuI-catalyzed Suzuki−Miyaura cross-coupling of vinyl halides and aryl halides with arylboronic acids was conducted smoothly to afford the corresponding diarylethenes and polyaryls in moderate to good yields using DABCO (1,4-diazabicyclo[2.2.2]octane) as the ligand. We also found that the inexpensive CuI/DABCO catalytic system was effective for Sonogashira cross-couplings of aryl halides

  在TBAB的存在下，使用DABCO（1,4-二氮杂双环[2.2。 2]辛烷）作为配体。我们还发现廉价的CuI / DABCO催化体系对于芳基卤化物和乙烯基卤化物的Sonogashira交叉偶联有效。各种芳基卤化物和乙烯基卤化物（包括活化的芳基氯化物）以中等至优异的产率与末端炔烃偶合。
• Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles with Alkynes Assisted by Lewis Acids: Efficient Synthesis of Fused Pyridines
  作者：Xu You、Xin Xie、Gaonan Wang、Meijun Xiong、Renhong Sun、Haoyi Chen、Yuanhong Liu

  DOI：10.1002/chem.201603829

  日期：2016.11.14

  A Ni/BPh3 catalyzed [2+2+2] cycloaddition of alkyne‐nitriles with alkynes has been developed, which provides an efficient route to fused pyridines under mild reaction conditions. Mechanistic studies indicate that an azanickelacycle via heterocoupling of an alkyne with a nitrile moiety is possibly formed as a key reaction intermediate. The Lewis acid catalyst is crucial to the successful transformation

  已开发出Ni / BPh 3催化炔烃与炔烃的[2 + 2 + 2]环加成反应，这为在温和的反应条件下合成熔融吡啶提供了一条有效途径。机理研究表明，可能通过炔烃与腈部分的异质偶联形成氮杂氮杂环作为关键反应中间体。路易斯酸催化剂对于成功的转化至关重要，这被认为可以促进氧化环化过程。
• Copper-catalyzed coupling reaction of aryl and vinyl halides with terminal alkynes
  作者：Kazumi Okuro、Makoto Furuune、Masahiro Miura、Masakatsu Nomura

  DOI：10.1016/s0040-4039(00)79093-9

  日期：1992.9

  Coupling reaction of aryl and vinyl halides with terminal alkynes using a catalyst system of copper(I) iodide - triphenylphosphine proceeds efficiently in the presence of potassium carbonate to give the corresponding unsymmetrical acetylenes in good yield.

  在碳酸钾的存在下，使用碘化铜（I）-三苯基膦的催化剂体系，芳基卤化物和乙烯基卤化物与末端炔烃的偶联反应有效地进行，从而以良好的收率得到相应的不对称乙炔。
• Cross-coupling of organosilanes with organic halides mediated by a palladium catalyst and tris(diethylamino)sulfonium difluorotrimethylsilicate
  作者：Yasuo Hatanaka、Tamejiro Hiyama

  DOI：10.1021/jo00239a056

  日期：1988.2
• Enyne synthesis through a modified Sonogashira cross-coupling reaction catalyzed by cyclopalladated complexes
  作者：Mengmeng Huang、Yujian Feng、Yangjie Wu

  DOI：10.1016/j.tet.2011.09.110

  日期：2012.1

  A series of conjugated enynes were successfully synthesized by the palladacycle-catalyzed modified Sonogashira cross-coupling reaction of beta-bromostyrene and terminal alkynes. The reaction proceeds smoothly in DMSO at 40 degrees C to give the corresponding products in moderate to excellent yields. This catalytic system is tolerant to a broad range of functional groups on the substrates. Moreover, the products were furnished as specific E isomers. We also found that the product of the reaction between (E)-beta-bromostyrene and 2-methyl-3-butyn-2-ol is diarylated enyne in the presence of excess Cs2CO3. (C) 2011 Elsevier Ltd. All rights reserved.